Date After Work 4 - Better not Rush This

"Alright, tell me when it's too uncomfortable, yeah?" says Zoey, kneeling behind you on the mattress, gently running her fingers over your ass.

"Mhm." you mumble back, lying on your stomach, trying to mentally prepare for the uncharted territory ahead (or, like, aback). You hear the splurt of the lube bottle being squeezed.

"Oh and just a heads-up: it's gonna be cold at first."

"Girl, I know what lube feels like." you snort, trying to relieve some tension. Zoey's done a lot in comparison but still, you're not *that* inexperiened.

"Fair enough." she chuckles and presses the tip of her lubed up finger against... well, the target. You reflexively tighten at the touch.

"Nonono, relax. Like, *actively* relax." advises Zoey and you do as you're told. You take a deep breath and actively make an effort to relax back there.

"That's a good girl." praises Zoey and presses her index finger a little harder. The muscle gives and lets her pass. You immediately grit your teeth in... not all that much discomfort actually. Huh.

"So far so good, yeah?" Zoey checks, her other hand rubbing a soothing pattern along your thigh.

"Actually yeah." you answer, quite pleasantly surprised. Then you prop yourself up on your elbows and look back over your shoulder. "Honestly, I thought this would be way- hoo!"

Zoey interrupts your sentence with a laugh by pushing her finger a bit deeper. "That was just the tip of one finger, princess. Don't get ahead of yourself."

"Oh shut up." you scoff and turn back forward, hiding the blush that's rising on your cheeks. That sudden increase in depth didn't even hurt, it was merely a tad uncomfortable due to its suddenness. At the same time, though, not too bad as well.

"I'mma move a lil'." announces Zoey and does exactly that. She carefully pulls her finger back a little and slides it back in, repeating the motion a few times. It feels really weird. Sooo different from vaginal, holy shit. No pain, some unease, but mostly odd. But it also has something nice to it. Maybe this has potential.

"Ready for another?" asks Zoey after a minute or so.

"Sure." you confirm without much hesitation. This has been far easier than expected!

"Damn, okay." chuckles your girlfriend, seemingly a bit surprised by the swiftness of your approval. A moment later, a second finger is pressing against your entrance. Okay, this is already a big difference.

"Deep breath." suggests Zoey and you comply. On the exhale, the additional finger enters. Oh, damn. Now that's a stretch.

"No clenching, Ronya." Zoey reminds you, patting your hip. "Relaaax."

You continue to follow her instructions. Sure, the added width is a bit of a stretch, but it's nothing you can't handle. Also, the longer she moves her two fingers around, the more the intrusion becomes managle and even pleasurable. It creates this kinda nice overall pressure in your general lower region.

"There we go." you hear Zoey behind you before feeling a kiss onto your right buttcheek. At the same time, she starts scissoring her fingers inside of you. You notice how little additional hurt the motions cause since it's not widening the... the entrance, so to speak. Zoey seems to do a very decent job at easing you into this (or easing herself into you, for that matter), which is ironic since she herself hasn't even had anything in her butt before.

"Okay, so when you manage a third one, I'd say we can try the real deal." says Zoey, still stretching and prodding your rear. Oh, shit. Like, a third finger is one thing - you can kinda guess how that's gonna feel like now - but a whole dick? HER big ass dick??

"Oookay, we'll see." you reply, the trepidation clearly audible in your voice.

"Hey, no worries. We can stop whenever." she assures you and places another peck onto your cheek. Strange how comforting a kiss on your ass can be.

"We'll see. Now gimme the third." you demand, deciding for some playfulness to ease your own tension.

"As my lady commands." Zoey audibly grins and removes her hand, presumably applying a fresh load of lube. A few seconds later, her fingers are back knocking at your door, just one more. The gently pushes in. Oof, okay. Okay, so far so good. Going from two to three seems easier than from one to two.

"All good?" checks Zoey and her free hand returns to your butt, kneading away.

"Y-yeah. Move a little." you request and she does, causing a faint burn, added to the sea of new sensations. That's a whole lot of pressure applied to that area. As a matter of fact, you even feel some of it travel to the front and stimulate your pussy. Well, not a full-on stimulation, but a nice little extra. This added to vaginal stuff? Okay, you can really see the vision.

"You know, you're taking this surprisingly well." comments Zoey, starting to push her fingers in and out a bit faster. "You might be a natural, heh."

"Finally... I found my true calling." you groan with a hint of panting.

"Haha, always love helping girl to discover their talents." jokes Zoey and stops fingering, instead opting to leave her fingers in and simply spread them a couple of times. "You ready for the real deal?"

"Well... ain't gonna get any readier." you decide, deeming your ability to deal with three fingers up your butt hopefully enough to manage her dick. Honestly though, despite your nervousness and the weird sensation, her prodding and stretching have managed to arouse you quite a bit. Plus you were obviously extremely horny to begin with, before that whole period debacle started. All of that might cloud your judgement a litte but you're in real mood for her dick. Realistically, how bad could it be?